So There’s That, Day 11: Scariest Day Ever

So There’s That: Adventures in Transgendering chronicled my transition in 2014. One hopes the gentle readers will forgive any awkward or anachronistic language within.

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Today is the day. The day I start telling people I’m transgender.

And I am terrified.

It begins with an early morning breakfast with an old friend from my days at AOL. She was a coworker, a boss, then I replaced her as boss when she moved on to bigger and better things. But most importantly, she’s a friend. That said, I haven’t seen her in person in something like seven years.

We meet at a small cafe and she looks fantastic. We chit chat for a bit, and I tell her I have some news. Big news. I’m scared and grinning at the same time, but dive into my little spiel.

I take a deep breath and with a wry smile, spit out, I’m transgender.

Her reaction brings tears to my eyes. She is beamingly happy for me. Thrilled. I think I’m going through a mini bout of post-traumatic stress after 40 years of secrets, shame and denial, but the happiness in her eyes, her unbridled joy, her love, carry me through the moment.

We talk about the joys of yoga pants, crying jags brought on by hormones, overly sensitive nipples. She asks me a million questions and it’s awesome. We are both SO overjoyed and I am SO relieved.

Welcome to the club, she says and I can’t remember the last time I was this happy. After all these years of shame, secrets and hiding, I’m being accepted for who I am. And it’s awesome.

An hour passes and we both need to run, but she gives me a long hug and tells me I’m going to have an amazing year. I smile through wet eyes and realize she’s right. I’ve been so caught up in THIS moment of revelation that I haven’t really thought about the future. Deep breath.

We part closer than when we met and I am over the moon.

But I have another morning meeting, this time with a guy I used to consult for. Another coffee does wonders for my nerves and as we catch up, he let’s me know he would love to work with me again.

I wasn’t planning on sharing my news, my big news. A few close friends and see where it goes.

But this is tear-off-the-band-aid time. Hell, it’s tear-off-the-damn-scab time.

So I tell him and he doesn’t blink. Literally. But he is genuinely happy for me and tells me the offer still stands. I try to explain that I’m still figuring things out, but I’m happy to show up to meetings in boy mode, this is business after all with paying clients — and he cuts me off.

No. You need to be who you are.

I am so blown away. I mean, first off, two-for-two. Second off, unconditional support I had never believed was possible.

I thank him from the bottom of my heart and make him promise to keep this under his hat for another week until I can tell his business partner who I’ve known for 15 years. I don’t want people finding out through the grapevine. I want to let them learn about my journey on my terms, so they can see how genuine I am at this crossroad in my life.

I mean, it’s not like a midlife crisis choice between being transgender or, say, buying a motorcycle. Hmmmm… heels or a Harley? I’ll chose the heels.

We shake hands in a most manly way and I hop the subway back to my office, realizing suddenly I’m committed. I mean, I’ve really gone public with this. Screw band-aids and scabs. I’ve just jumped off the the damn cliff.

I get to my office and three of my coworkers are there. No time like the present, right?

It feels a little like a movie montage, only it’s my life…

Colleague #1: I’m still nervous. I’m still REALLY nervous as I’m about to tell someone with whom I’ve worked all-nighters for the past three years. I mean, I know he’ll be supportive. But I don’t know he’ll be supportive, if that makes sense. Despite having quit smoking some time ago, I ask if he wants to go out for a smoke. I do my little little dance, big breath, and tell him. He grins and tells me how happy he is for me. Big hug. Another deep breath. Hell, another cigarette. I go into more details, but I am starting to sense guys just want to be happy for me and move on to fantasy football. We end with a handshake, another manly handshake, and talk about our fantasy football starters for the week.

Colleague #2: One would think it’d be getting a bit easier by now, but it isn’t. My next reveal is with someone I hired a few years back, a woman. A cis woman. Again, I know she’ll be supportive, but there’s always that doubt in the back of your mind. As I gather up my courage, she tells me to take a deep breath. Yeah, definitely not easier. Deep breath and I come clean. She smiles broadly and tells me how fantastic it is that I’m coming out. We chat for a little more and she tells me if there is anything I ever need, just to ask. No handshake this time, but I’ll definitely be asking her for makeup tips in the future. She has some of the best makeup I’ve seen, period. #jealous

Colleague #3: One more and I’m done with NYC for the day. Maybe because we haven’t worked together for all that long, this one is a little easier. Again, he takes it in stride. Is very happy for me. We share a few personal details on life struggles. Handshake. Fantasy football.

Five for five. Not too shabby. But all I want to do is to crawl into the bathroom and cry. I am SO emotionally spent. I decide to head home early, thank everyone for their wonderful support and make a beeline to the train back to Maryland.

Once on the train, I realize I can’t break down with a person sitting next to me. And Amtrak bathrooms do not good crying chambers make. I finally get back to my car and dissolve into tears. There is a mixture of a) have you lost your freakin’ mind! b) you have the best friends EVER! c) have you lost your FREAKIN’ mind! and d) you can do this.

I drive home and realize I have one more person to tell tonight. My youngest child, who, perhaps, isn’t so young anymore being 17 years old and all.

But let’s leave THAT little bit of terror for tomorrow.